There is no movie that better portrays fall fashion in New York City than famed 80’s romantic comedy When Harry Met Sally.

Not only was the movie’s fashion styling choices remarkably memorable, but so were its characters. From Meg Ryan’s big, baby blue eyes to Billy Crystal’s sense of humor, there is hardly a reason to not be moved by the movie’s plot of undiscovered love in the city.

But back to fashion. Every fall, fashion magazines talk about layering, menswear, and nature-inspired color schemes as trends that keep coming back during this time of the year.

New Yorkers are known for walking everywhere, and Sally’s choice of shoe was a wide range that included dapper brogues, leather loafers, and sturdy low-heeled boots.

Her taste in clothing is practical and masculine, but when worn on her long, lean frame and fused with quirky embellishments like a silk bow tie or funny print, her look is effortless, relatable, and totally chic.